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More than likely the teeth are chewed up as you suspect. My 250 did the same thing, despite the new shift levers seeming to tighten up properly upon intial installation.

Changing the shaft is actually not much worse than replacing a clutch. You do not have to split the cases, but you do have to pull the clutch basket, as the fork on the end of the shift shaft is behind the basket. Not required, but it's a good time to replace the shift shaft seal while you are at it. All in all, it is an easy job and fairly inexpensive. Make sure you install a fresh shift lever; don't use one that has been mounted on the defective splines.

The best way to prevent this is to keep your shift lever tight by checking it periodically.